Abstract |
Two Ru(II) polypyridyl-porphyrin and Zn(II) porphyrin conjugates (Ru-L and Ru-Zn-L) have been synthesized and their photophysical properties studied. The two conjugates, which contained a hydrophobic tetraphenylporphyrin L conjugated via an acetylide linker at its β-position with a hydrophilic Ru(II) polypyridyl complex, showed high singlet oxygen quantum yields (>70%) and substantial two-photon absorption cross-sections (~500 GM). Ru-L gave strong emissions at ~660 and ~733 nm through linear or two-photon excitation. Solvatochromism was observed in the fluorescence spectra of Ru-L and Ru-Zn-L, where in less polar solvents (i.e., toluene and dichloromethane) their fluorescence emissions became slightly blue-shifted with a 3-fold reduction in intensity relative to those observed in polar solvents (i.e., acetonitrile and methanol). Cell-based studies of these complex conjugates were conducted using human nasopharyngeal carcinoma HK-1 and cervical carcinoma HeLa cells on which Ru-L showed rapid cellular uptake, low dark-cytotoxicity, and high photo-cytotoxicity. Furthermore, Ru-L can be excited and emits in the "biological window"in vitro, making it a potential potent new generation photodynamic therapeutic agent capable of singlet oxygen generation and in vitro near-infrared emission.
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Authors | JingXiang Zhang, Ka-Leung Wong, Wai-Kwok Wong, Nai-Ki Mak, Daniel W J Kwong, Hoi-Lam Tam |
Journal | Organic & biomolecular chemistry
(Org Biomol Chem)
Vol. 9
Issue 17
Pg. 6004-10
(Sep 07 2011)
ISSN: 1477-0539 [Electronic] England |
PMID | 21748193
(Publication Type: Journal Article, Research Support, Non-U.S. Gov't)
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Chemical References |
- Antineoplastic Agents
- Cytotoxins
- Metalloporphyrins
- Photosensitizing Agents
- Ru(II) polypyridyl-porphyrin
- Ru-Zn-polypyridyl-porphyrin
- Singlet Oxygen
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Topics |
- Antineoplastic Agents
(chemistry, pharmacokinetics, pharmacology)
- Cell Line, Tumor
- Cytotoxins
(chemistry, pharmacokinetics, pharmacology)
- Humans
- Luminescence
- Metalloporphyrins
(chemistry, pharmacokinetics, pharmacology)
- Neoplasms
(drug therapy)
- Photochemotherapy
- Photosensitizing Agents
(chemistry, pharmacokinetics, pharmacology)
- Singlet Oxygen
(metabolism)
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